The Athletic's Ken Rosenthal spoke to a source on July 17 who said Chapman will "one million percent" opt out of his five-year, $86 million deal. However, MLB Network's Jon Heyman reported Friday the six-time All-Star prefers signing a long-term extension with the Yankees.
Clayton Kershaw did something similar with the Los Angeles Dodgers this past offseason. Although he didn't formally opt out and become a free agent, he basically voided his existing contract and re-signed with L.A. for three years and $93 million.
CC Sabathia signed a five-year, $122 million deal with the Yankees in 2011, which ultimately meant getting one more guaranteed season from New York, when he was approaching the deadline to opt out from his contract.
Based on how the 2020 market looks for relievers, Chapman could presumably leverage his opt-out to get improved terms with the Yankees.
Dellin Betances, Liam Hendriks and Will Smith are all free agents, with Smith the only one of the three with a lot of experience in the closer role. Sean Doolittle has a $6.5 million team option that the Washington Nationals will almost assuredly exercise. Like Chapman, Kenley Jansen can opt out but might struggle to match the $38 million he'll earn in 2020 and 2021 based on his performance this season.
Chapman remains one of MLB's best closers. He has 26 saves, 56 strikeouts, 17 walks and a 2.42 FIP in 39.2 innings pitched, per Baseball Reference.
The left-hander turns 32 in February. It makes sense for him to use every tool at his disposal this winter to maximize his earning power.